Please use this identifier to cite or link to this item: http://dx.doi.org/10.25673/115575
Title: Structural characterization of a 3-hydroxychromone dye trehalose conjugate for fluorescent labelling of mycobacteria
Author(s): Richter, AdrianLook up in the Integrated Authority File of the German National Library
Goddard, Richard W.Look up in the Integrated Authority File of the German National Library
Brinkmann, LeaLook up in the Integrated Authority File of the German National Library
Siersleben, Fabienne
Seidel, Rüdiger W.Look up in the Integrated Authority File of the German National Library
Issue Date: 2024
Type: Article
Language: English
Abstract: 3-Hydroxychromone (3HC) dye trehalose conjugates have previously been exploited as environment-sensitive fluorescent labels to detect mycobacteria by fluorescence microscopy. We have studied the 3HC dye 2-(6-(diethylamino)benzofuran-2-yl)-3-hydroxy-4H-chromen-4-one (3HC-2) trehalose conjugate 3HC-2-Tre by X-ray crystallography, spectroscopic methods augmented by DFT calculations and conducted preliminary labelling experiments with Mycobacterium abscessus, a non-tuberculous mycobacterium and opportunistic pathogen. In the crystal structure of 3HC-2-Tre ⋅ 3.14 H2O, the 3HC-2-Tre molecules exhibit an intramolecular Osingle bondH⋅⋅⋅O hydrogen bond between the 5-hydroxy group of trehalose and the chromone carbonyl oxygen atom, and form hydrogen-bonded dimers via the trehalose units with approximate local C2 symmetry. The chromophore adopts an s-cis conformation of the chromone and benzofuran systems about its central Csingle bondC bond, as previously encountered in the crystal structure of the free dye 3HC-2, and the trehalose moieties approximately retain the shape as found in the crystal structures of anhydrous trehalose and the dihydrate. Absorption spectra of 3HC-2-Tre acquired in four different solvents revealed small positive solvatochromy. Fluorescence microscopy detected M. abscessus cells treated with 3HC-2-Tre in the GFP channel.
URI: https://opendata.uni-halle.de//handle/1981185920/117528
http://dx.doi.org/10.25673/115575
Open Access: Open access publication
License: (CC BY-NC-ND 4.0) Creative Commons Attribution NonCommercial NoDerivatives 4.0(CC BY-NC-ND 4.0) Creative Commons Attribution NonCommercial NoDerivatives 4.0
Journal Title: Journal of molecular structure
Publisher: Elsevier
Publisher Place: New York, NY [u.a.]
Volume: 1298
Issue: Part 2
Original Publication: 10.1016/j.molstruc.2023.137010
Page Start: 1
Page End: 8
Appears in Collections:Open Access Publikationen der MLU

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